Synthesis of Pyrrolo[2,1‑a]isoquinolines through Cu-Catalyzed Condensation/Addition/Oxidation/Cyclization Cascade

Synthesis of Pyrrolo[2,1‑a]isoquinolines through Cu-Catalyzed Condensation/Addition/Oxidation/Cyclization Cascade

We have developed a copper-catalyzed synthesis of pyrrolo­[2,1-a]­isoquinolines with terminal alkynes, aldehydes, and tetrahydroisoquinolines. A variety of pyrrolo­[2,1-a]­isoquinolines have been prepared in 17–69% yield via a condensation/Mannich-type addition/oxidation/cyclization cascade sequence...

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Veröffentlicht in:Journal of organic chemistry 2022-11, Vol.87 (22), p.15435-15447
Hauptverfasser: Cui, Hai-Lei, Chen, Xiao-Hui
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Catalysis
Copper - chemistry
Cyclization
Isoquinolines - chemistry
Molecular Structure
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Zusammenfassung:We have developed a copper-catalyzed synthesis of pyrrolo­[2,1-a]­isoquinolines with terminal alkynes, aldehydes, and tetrahydroisoquinolines. A variety of pyrrolo­[2,1-a]­isoquinolines have been prepared in 17–69% yield via a condensation/Mannich-type addition/oxidation/cyclization cascade sequence. Modifications through simple chemical transformations provided highly functionalized molecules containing a privileged framework.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01978